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2000•European Journal of Organic ChemistryRequires access

Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

Arata Yajima, Kenji Mori

Open publisher page 55 citations

Abstract

To determine the absolute configuration of the phytocassane group of phytoalexins, the naturally occurring (−)-phytocassane D was synthesized from the (R)-Wieland−Miescher ketone, in an approach based on the preliminary model synthesis of the unnatural (+)-2-deoxyphytocassane A. By comparison of their CD spectra with those of synthetic phytocassanes of known absolute configuration, phytocassanes A−E were shown to possess the ent-cassane skeleton.

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What this paper is about

To determine the absolute configuration of the phytocassane group of phytoalexins, the naturally occurring (−)-phytocassane D was synthesized from the (R)-Wieland−Miescher ketone, in an approach based on the preliminary model synthesis of the unnatural (+)-2-deoxyphytocassane A. By comparison of their CD spectra with those of synthetic phytocassanes of known absolute configuration, phytocassanes A−E were shown to possess the ent-cassane skeleton.

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Available abstract

To determine the absolute configuration of the phytocassane group of phytoalexins, the naturally occurring (−)-phytocassane D was synthesized from the (R)-Wieland−Miescher ketone, in an approach based on the preliminary model synthesis of the unnatural (+)-2-deoxyphytocassane A. By comparison of their CD spectra with those of synthetic phytocassanes of known absolute configuration, phytocassanes A−E were shown to possess the ent-cassane skeleton.

Key concepts: Absolute configuration, Diterpene, Phytoalexin, Chemistry, Stereochemistry, Oryza sativa, Absolute (philosophy), Ketone

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Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa — Research Paper | ScholarLens